2.0 2012-07-30 14:54:38 -0600 2015-06-03 17:20:38 -0600 ECMDB21104 M2MDB001513 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) 1,2-diacyl-sn-glycerol (dihexadec-9-enoyl, n-c16:1) belongs to the class of Diacylglycerols. These are glycerides consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. (inferred from compound structure) (2S)-2-(Z)-hexadec-9-enoyloxy-3-hydroxypropyl (Z)-hexadec-9-enoate (2S)-2-(Z)-Hexadec-9-enoyloxy-3-hydroxypropyl (Z)-hexadec-9-enoic acid C35H64O5 564.8797 564.475375158 (2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (9Z)-hexadec-9-enoate diacylglycerol [H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC InChI=1S/C35H64O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(37)39-32-33(31-36)40-35(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,33,36H,3-12,17-32H2,1-2H3/b15-13-,16-14-/t33-/m0/s1 HSQHRRHRYJNSOC-DWCRPSDDSA-N Membrane logp 9.63 ALOGPS logs -7.57 ALOGPS solubility 1.51e-05 g/l ALOGPS logp 11.28 ChemAxon pka_strongest_acidic 14.58 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (9Z)-hexadec-9-enoate ChemAxon average_mass 564.8797 ChemAxon mono_mass 564.475375158 ChemAxon smiles [H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC ChemAxon formula C35H64O5 ChemAxon inchi InChI=1S/C35H64O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(37)39-32-33(31-36)40-35(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,33,36H,3-12,17-32H2,1-2H3/b15-13-,16-14-/t33-/m0/s1 ChemAxon inchikey HSQHRRHRYJNSOC-DWCRPSDDSA-N ChemAxon polar_surface_area 72.83 ChemAxon refractivity 169.93 ChemAxon polarizability 72.16 ChemAxon rotatable_bond_count 32 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z)) "Phospholipids are membrane components in E. coli. The major phospholipids of E. coli are phosphatidylethanolamine, phosphatidylglycerol and cardiolipin. All phospholipids contain sn-glycerol-3-phosphate esterified with fatty acids at the sn-1 and sn-2 positions. The reaction starts from a glycerone phosphate (dihydroxyacetone phosphate) produced in glycolysis. The glycerone phosphate is transformed to a sn-glycerol 3-phosphate (glycerol 3 phosphate) by NADPH driven glycerol-3-phosphate dehydrogenase. Sn-glycerol 3-phosphate is transformed to a 1-acyl-sn-glycerol 3-phosphate(1-oleyl-2-lyso-phosphatidate , 1-palmitoylglycerol 3-phosphate , 1-stearoyl-sn-glycerol 3-phosphate). This can be achieve by a sn-glycerol-3-phosphate 1-0-acyltransferase that interacts either with a long-chain acyl-CoA or with an acyl-[acp]. The 1-acyl-sn-glycerol 3-phosphate is transformed into a 1,2-diacyl-sn-glycerol 3-phosphate through a 1-acylglycerol-3-phosphate O-acyltransferase. This compound is then converted into a CPD-diacylglycerol through a CTP (phosphatidate cytididyltransferase. CPD-diacylglycerol can be transformed either to a L-1-phosphatidylserine or a L-1-phosphatidylglycerol-phosphate through a phosphatidylserine synthase or a phosphatidylglycerophosphate synthase respectively. The L-1-phosphatidylserine transforms into L-1-phosphatidylethanolamine through a phosphatidylserine decarboxylase, o the other hand L-1-phosphatidylglycerol-phosphate gets transformed into a L-1-phosphatidyl-glycerol through a phosphatidylglycerophosphatase. These 2 products combines produce a cardiolipin and a ethanolamine. The L-1 phosphatidyl-glycerol can also interact with cardiolipin synthase resulting in a glycerol and a cardiolipin." PW001549 Metabolic Specdb::CMs 39250 Specdb::CMs 282098 Specdb::CMs 358990 Specdb::NmrOneD 289935 Specdb::NmrOneD 289936 Specdb::NmrOneD 289937 Specdb::NmrOneD 289938 Specdb::NmrOneD 289939 Specdb::NmrOneD 289940 Specdb::NmrOneD 289941 Specdb::NmrOneD 289942 Specdb::NmrOneD 289943 Specdb::NmrOneD 289944 Specdb::NmrOneD 289945 Specdb::NmrOneD 289946 Specdb::NmrOneD 289947 Specdb::NmrOneD 289948 Specdb::NmrOneD 289949 Specdb::NmrOneD 289950 Specdb::NmrOneD 289951 Specdb::NmrOneD 289952 Specdb::NmrOneD 289953 Specdb::NmrOneD 289954 Specdb::MsMs 640405 Specdb::MsMs 640406 Specdb::MsMs 640407 Specdb::MsMs 2421702 Specdb::MsMs 2421703 Specdb::MsMs 2421704 Specdb::MsMs 2513342 Specdb::MsMs 2513343 Specdb::MsMs 2513344 Specdb::MsMs 2889355 Specdb::MsMs 2889356 Specdb::MsMs 2889357 Specdb::MsMs 3033926 Specdb::MsMs 3033927 Specdb::MsMs 3033928 9543679 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A Phosphatidylglycerophosphatase B P0A924 PGPB_ECOLI pgpB http://ecmdb.ca/proteins/P0A924.xml Phosphatidate cytidylyltransferase P0ABG1 CDSA_ECOLI cdsA http://ecmdb.ca/proteins/P0ABG1.xml Diacylglycerol kinase P0ABN1 KDGL_ECOLI dgkA http://ecmdb.ca/proteins/P0ABN1.xml Phosphoethanolamine transferase eptB P37661 EPTB_ECOLI eptB http://ecmdb.ca/proteins/P37661.xml Water + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Phosphate KDO2-Lipid A + PE(14:0/14:0) > 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Phosphoethanolamine KDO(2)-lipid (A) 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0) 2 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Cytidine triphosphate + Hydrogen ion >2 CDP-1,2-dihexadec-9-enoylglycerol + Pyrophosphate PW_R005696